Jamaica debuted in the Gold Cup in 1991. In 10 appearances, the Reggae Boyz have been runners up twice, in 2015 and 2017. In their first participation, Jamaica lost 3-1 to Mexico at Lincoln Financial Field in Philadelphia, and in the second they lost 2-1 to the United States in Santa Clara, California. They were led by goalkeeper Andre Blake, who was named the tournament’s most valuable player in 2017. In Concacaf Nations League Qualifying, Jamaica finished in fifth place with Darren Mattocks leading the way with three goals. Mattocks is Jamaica’s all-time leading Gold Cup scorer with 4 goals.

Jamaica record in Gold Cup: GP- 41 W-16 D-7 L-18 GF-47 GA-59